Derivatives of caffeic acid, a natural antioxidant, as the basis for the discovery of novel nonpeptidic neurotrophic agents

Moosavi, Fatemeh; Hosseini, Razieh; Rajaian, Hamid; Silva, Tiago; Silva, Diogo Magalhães e; Saso, Luciano; Edraki, Najmeh; Miri, Ramin; Borges, Fernanda; Firuzi, Omidreza

doi:10.1016/j.bmc.2017.04.026

Cited by 26 publications

(15 citation statements)

References 45 publications

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“…Based on UHPLC-HRMS, one carboxylic acid, five phenolic acids, five acylquinic acids and two phenylethanoid glycosides were identified in A. aspera. Salicylic acid (33), caffeic acid (36), quinic acid (37) and ferulic acid (38) were found in all studied extracts. Chlorogenic acid (41), 3,5-dicaffeoylquinic acid (43) and 4,5-dicaffeoylquinic acid (44) were detected in all samples, while 4-caffeoylquinic acid (42) was observed only in dichloromethane and infused extracts.…”

Section: Carboxylic Phenolic and Acylquinic Acids Phenylethanoid Glmentioning

confidence: 84%

“…In fact, the antioxidant activities of some compounds identified in A. aspera extracts were reported in several studies. As example, some compounds such as protocatechuic acid, caffeic acid, chlorogenic acid, ferulic acid and gentisic acid are referred to as a powerful antioxidant [34][35][36][37]. Previously, Yeh and Yen [38] reported the significant induction of hepatic antioxidant enzyme by gentisic acid, caffeic acid and ferulic acid, following oral administration of these compounds to male Sprague-Dawley rats.…”

Section: Antioxidant and Enzyme Inhibitory Effectsmentioning

confidence: 99%

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Qualitative Phytochemical Fingerprint and Network Pharmacology Investigation of Achyranthes aspera Linn. Extracts

et al. 2020

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Achyranthes aspera Linn. (Amaranthaceae), commonly known as the Prickly Chaff flower, is used as herbal medicine in the Ivorian’s culture, Africa. Nonetheless, there is currently a paucity of scientific information on A. aspera from the Ivory Coast. Herein, the antioxidant activity of A. aspera extracts (methanol, dichloromethane, ethyl acetate and infusion) as well as the enzymatic inhibitory potentials towards key enzymes in human diseases, namely Alzheimer’s disease, (cholinesterases: AchE and BChE), type 2 diabetes (α-glucosidase and α-amylase) and hyperpigmentation (tyrosinase) were assessed. The total phenolic (TPC) and flavonoid (TFC) content was determined using colorimetric methods and the individual compounds were characterized using ultra-high performance liquid chromatography coupled with hybrid quadrupole-Orbitrap high resolution mass spectrometry (UHPLC-HRMS). Furthermore, a network pharmacology analysis was conducted to predict putative targets of identified phenolic compounds. The highest TPC was observed in the infused extract (28.86 ± 0.12 mg GAE/g), while the dichloromethane extract (38.48 ± 1.48 mg RE/g) showed the highest level of TFC. UHPLC-HRMS analysis has revealed an abundance of fatty acids, flavonoids, phenols and acylquinic acids. Among tested extracts, the infused extract displayed the highest free radical quenching, reducing and metal-chelating ability. The extracts (except infusion) were effective as enzyme inhibitors against AChE, while only methanolic and infused extracts showed noteworthy anti-BChE effects. The methanolic extract showed a remarkable antityrosinase effect (56.24 ± 5.05 mg KAE/g), as well. Modest to moderate inhibitory activity was observed against α-amylase (all extracts) and α-glucosidase (only dichloromethane extract). Finally, the network pharmacology analysis suggested the carbonic anhydrase II enzyme as a putative target for explaining, at least in part, the traditional use of A. aspera preparations as diuretic and blood clotting agent. Data amassed herein tend to validate the use of A. aspera in traditional medicine, as well as act as a stepping stone for further studies in the quest for novel phytopharmaceuticals. In this context, it is desirable that this study will contribute to the validation of the traditional uses of this plant in the African herbal medicine, and to the valorization of the whole chain production of A. aspera, as a local and sustainable botanical resource.

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Section: Carboxylic Phenolic and Acylquinic Acids Phenylethanoid Glmentioning

confidence: 84%

Section: Antioxidant and Enzyme Inhibitory Effectsmentioning

confidence: 99%

Qualitative Phytochemical Fingerprint and Network Pharmacology Investigation of Achyranthes aspera Linn. Extracts

et al. 2020

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“…Other investigators have even shown that intravitreal injection by a single dose is probably the best way to examine the direct effects of compounds on neurodegenerative changes in animal models of diabetic retinopathy . On the other hand, alkyl amide derivatives of CA have suitable drug‐like properties and therefore are appropriate for in vivo pharmacological studies …”

Section: Resultsmentioning

confidence: 99%

“…The neuroprotective effect of CA phenethyl ester has been shown in a range of neurodegenerative diseases . In previous studies of our research groups, it was observed that a series of ester, and amide analogs of CA with variable alkyl chain lengths showed strong neuroprotection in in vitro models via modulation of neuronal signaling pathways. Among these synthesized derivatives, hexyl and dodecyl amide derivatives of CA, which were among the most efficient compounds, were chosen for further studies.…”

Section: Introductionmentioning

confidence: 91%

Caffeic Acid Alkyl Amide Derivatives Ameliorate Oxidative Stress and Modulate ERK1/2 and AKT Signaling Pathways in a Rat Model of Diabetic Retinopathy

Fathalipour

Eghtedari

Borges

et al. 2019

Chemistry & Biodiversity

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The purpose of this study was to examine the neuroprotective effects of caffeic acid hexyl (CAF6) and dodecyl (CAF12) amide derivatives on the early stage of retinopathy in streptozotocin-induced diabetic rats. Animals were divided in five groups (n = 8/group); one group consisted of non-diabetic rats as control, while the other four were diabetic animals either non-treated or treated with CAF6, CAF12 or resveratrol intravitreally for four weeks. Retinal superoxide dismutase (SOD) activity and 8-iso-prostaglandin F 2α (iPF 2α ) levels were evaluated by an ELISA assay. Phosphorylation of ERK1/2 and AKT was determined by immunoblotting in retinal homogenates. Retinal morphology was also examined using light microscopy. Treatment with CAF6 and CAF12 increased retinal SOD activity, while it decreased iPF 2α levels in diabetic rats. Phosphorylation of ERK1/2 was increased, while AKT phosphorylation was decreased in diabetic rats compared to normal control and these alterations were significantly reversed in diabetic rats treated with CAF6 and CAF12. Furthermore, thickness of the whole retinal layer, outer nuclear layer, and ganglion cell count were decreased in diabetic rats compared to control and CAF6 and CAF12 treatments prevented these changes. CAF6 and CAF12 seem to be effective agents for treatment of diabetic retinopathy via attenuation of retinal oxidative stress and improvement of neuronal survival signaling.

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“…These findings have established that CAPE is a potent bioactive compound and could instigate multiple molecular responses in treated cell/animal models. Moreover, recent findings on caffeic acid derivatives have shown its neurogenesis and neuroprotection function (Fu et al, 2013 ; Moosavi et al, 2017 ), however, its underlying cellular and molecular mechanisms remain elusive.…”

Section: Introductionmentioning

confidence: 99%

Identification of Caffeic Acid Phenethyl Ester (CAPE) as a Potent Neurodifferentiating Natural Compound That Improves Cognitive and Physiological Functions in Animal Models of Neurodegenerative Diseases

Konar

Kalra

Chaudhary

et al. 2020

Front. Aging Neurosci.

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Derivatives of caffeic acid, a natural antioxidant, as the basis for the discovery of novel nonpeptidic neurotrophic agents

Cited by 26 publications

References 45 publications

Qualitative Phytochemical Fingerprint and Network Pharmacology Investigation of Achyranthes aspera Linn. Extracts

Qualitative Phytochemical Fingerprint and Network Pharmacology Investigation of Achyranthes aspera Linn. Extracts

Caffeic Acid Alkyl Amide Derivatives Ameliorate Oxidative Stress and Modulate ERK1/2 and AKT Signaling Pathways in a Rat Model of Diabetic Retinopathy

Identification of Caffeic Acid Phenethyl Ester (CAPE) as a Potent Neurodifferentiating Natural Compound That Improves Cognitive and Physiological Functions in Animal Models of Neurodegenerative Diseases

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